CN105493310A - Resin composition for gasket, production method therefor, and gasket for secondary battery - Google Patents
Resin composition for gasket, production method therefor, and gasket for secondary battery Download PDFInfo
- Publication number
- CN105493310A CN105493310A CN201480048085.9A CN201480048085A CN105493310A CN 105493310 A CN105493310 A CN 105493310A CN 201480048085 A CN201480048085 A CN 201480048085A CN 105493310 A CN105493310 A CN 105493310A
- Authority
- CN
- China
- Prior art keywords
- pad
- polyarylene sulfide
- sulfide resin
- resin combination
- resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 29
- 239000011342 resin composition Substances 0.000 title abstract description 10
- 229920005989 resin Polymers 0.000 claims abstract description 111
- 239000011347 resin Substances 0.000 claims abstract description 111
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 68
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims abstract description 60
- 229920000412 polyarylene Polymers 0.000 claims abstract description 60
- 238000000034 method Methods 0.000 claims abstract description 41
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000003112 inhibitor Substances 0.000 claims abstract description 34
- 239000000203 mixture Substances 0.000 claims abstract description 32
- 239000003792 electrolyte Substances 0.000 claims abstract description 13
- -1 amino, carboxyl Chemical group 0.000 claims description 39
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 20
- 238000002156 mixing Methods 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 230000004888 barrier function Effects 0.000 claims description 5
- 238000005227 gel permeation chromatography Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 abstract description 32
- 150000001875 compounds Chemical class 0.000 abstract description 23
- 239000000463 material Substances 0.000 abstract description 13
- 229920001296 polysiloxane Polymers 0.000 abstract description 4
- 238000003860 storage Methods 0.000 abstract description 4
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 abstract description 3
- 229910001416 lithium ion Inorganic materials 0.000 abstract description 3
- 150000001491 aromatic compounds Chemical class 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 238000007789 sealing Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 23
- 239000012065 filter cake Substances 0.000 description 21
- 239000004734 Polyphenylene sulfide Substances 0.000 description 19
- 229920000069 polyphenylene sulfide Polymers 0.000 description 19
- 229910052740 iodine Inorganic materials 0.000 description 16
- 239000011630 iodine Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000012298 atmosphere Substances 0.000 description 10
- 125000000524 functional group Chemical group 0.000 description 10
- 239000007789 gas Substances 0.000 description 10
- 230000003252 repetitive effect Effects 0.000 description 10
- 229910000077 silane Inorganic materials 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 238000013329 compounding Methods 0.000 description 8
- 239000000835 fiber Substances 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 238000005342 ion exchange Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 230000006835 compression Effects 0.000 description 6
- 238000007906 compression Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 230000001590 oxidative effect Effects 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 150000003568 thioethers Chemical group 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 238000010276 construction Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000001746 injection moulding Methods 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000007493 shaping process Methods 0.000 description 4
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 230000002787 reinforcement Effects 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 125000005353 silylalkyl group Chemical group 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 2
- NQMUGNMMFTYOHK-UHFFFAOYSA-N 1-methoxynaphthalene Chemical compound C1=CC=C2C(OC)=CC=CC2=C1 NQMUGNMMFTYOHK-UHFFFAOYSA-N 0.000 description 2
- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229910052582 BN Inorganic materials 0.000 description 2
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000005362 aryl sulfone group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- DWNAQMUDCDVSLT-UHFFFAOYSA-N diphenyl phthalate Chemical compound C=1C=CC=C(C(=O)OC=2C=CC=CC=2)C=1C(=O)OC1=CC=CC=C1 DWNAQMUDCDVSLT-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- 150000002220 fluorenes Chemical class 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 230000008676 import Effects 0.000 description 2
- 239000012778 molding material Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 150000005181 nitrobenzenes Chemical class 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical group C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 238000012958 reprocessing Methods 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 229920005573 silicon-containing polymer Polymers 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 230000003381 solubilizing effect Effects 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QQFIQWBUKYSUHM-UHFFFAOYSA-N (2,3-diiodophenyl)-phenylmethanone Chemical compound IC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1I QQFIQWBUKYSUHM-UHFFFAOYSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 description 1
- DBNWBEGCONIRGQ-UHFFFAOYSA-N 1,1-diphenylpropan-2-one Chemical compound C=1C=CC=CC=1C(C(=O)C)C1=CC=CC=C1 DBNWBEGCONIRGQ-UHFFFAOYSA-N 0.000 description 1
- LSESTAVEDKBXPP-UHFFFAOYSA-N 1,2-diiodo-3,4-dimethylbenzene Chemical compound CC1=CC=C(I)C(I)=C1C LSESTAVEDKBXPP-UHFFFAOYSA-N 0.000 description 1
- BBOLNFYSRZVALD-UHFFFAOYSA-N 1,2-diiodobenzene Chemical compound IC1=CC=CC=C1I BBOLNFYSRZVALD-UHFFFAOYSA-N 0.000 description 1
- UYHYZAYIQAVJCN-UHFFFAOYSA-N 1,2-diiodonaphthalene Chemical compound C1=CC=CC2=C(I)C(I)=CC=C21 UYHYZAYIQAVJCN-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- YFKBXYGUSOXJGS-UHFFFAOYSA-N 1,3-Diphenyl-2-propanone Chemical compound C=1C=CC=CC=1CC(=O)CC1=CC=CC=C1 YFKBXYGUSOXJGS-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- LVUQCTGSDJLWCE-UHFFFAOYSA-N 1-benzylpyrrolidin-2-one Chemical compound O=C1CCCN1CC1=CC=CC=C1 LVUQCTGSDJLWCE-UHFFFAOYSA-N 0.000 description 1
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 1
- GPYDMVZCPRONLW-UHFFFAOYSA-N 1-iodo-4-(4-iodophenyl)benzene Chemical group C1=CC(I)=CC=C1C1=CC=C(I)C=C1 GPYDMVZCPRONLW-UHFFFAOYSA-N 0.000 description 1
- SCCCFNJTCDSLCY-UHFFFAOYSA-N 1-iodo-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(I)C=C1 SCCCFNJTCDSLCY-UHFFFAOYSA-N 0.000 description 1
- IYDMICQAKLQHLA-UHFFFAOYSA-N 1-phenylnaphthalene Chemical compound C1=CC=CC=C1C1=CC=CC2=CC=CC=C12 IYDMICQAKLQHLA-UHFFFAOYSA-N 0.000 description 1
- JMVIVASFFKKFQK-UHFFFAOYSA-N 1-phenylpyrrolidin-2-one Chemical compound O=C1CCCN1C1=CC=CC=C1 JMVIVASFFKKFQK-UHFFFAOYSA-N 0.000 description 1
- VALABLHQPAMOBO-UHFFFAOYSA-N 2,4-diiodo-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(I)C=C1I VALABLHQPAMOBO-UHFFFAOYSA-N 0.000 description 1
- DCJKUXYSYJBBRD-UHFFFAOYSA-N 2,5-diphenyl-1,3,4-oxadiazole Chemical class C1=CC=CC=C1C1=NN=C(C=2C=CC=CC=2)O1 DCJKUXYSYJBBRD-UHFFFAOYSA-N 0.000 description 1
- CNRNYORZJGVOSY-UHFFFAOYSA-N 2,5-diphenyl-1,3-oxazole Chemical compound C=1N=C(C=2C=CC=CC=2)OC=1C1=CC=CC=C1 CNRNYORZJGVOSY-UHFFFAOYSA-N 0.000 description 1
- AHKDVDYNDXGFPP-UHFFFAOYSA-N 2,6-dimethoxynaphthalene Chemical compound C1=C(OC)C=CC2=CC(OC)=CC=C21 AHKDVDYNDXGFPP-UHFFFAOYSA-N 0.000 description 1
- ATGFTMUSEPZNJD-UHFFFAOYSA-N 2,6-diphenylphenol Chemical compound OC1=C(C=2C=CC=CC=2)C=CC=C1C1=CC=CC=C1 ATGFTMUSEPZNJD-UHFFFAOYSA-N 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
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- 239000010936 titanium Substances 0.000 description 1
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- 125000003944 tolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M50/00—Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
- H01M50/10—Primary casings; Jackets or wrappings
- H01M50/183—Sealing members
- H01M50/19—Sealing members characterised by the material
- H01M50/193—Organic material
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/06—Sulfur
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/02—Polythioethers; Polythioether-ethers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M50/00—Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
- H01M50/10—Primary casings; Jackets or wrappings
- H01M50/183—Sealing members
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M50/00—Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
- H01M50/10—Primary casings; Jackets or wrappings
- H01M50/183—Sealing members
- H01M50/184—Sealing members characterised by their shape or structure
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
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Abstract
Provided are: a resin composition for a gasket, said resin composition being used as a material for a gasket used in a sealed secondary battery (storage battery) such as a lithium ion secondary battery, and exhibiting excellent cavity balance and a high mechanical strength; a production method for said resin composition; and a gasket for a secondary battery. More specifically, the present invention relates to: a resin composition for a gasket used in a secondary battery configured from a positive electrode, a negative electrode, a sealing body, a gasket, a separator, and an electrolyte, said resin composition including a polyarylene sulfide resin and a silicone compound, and being capable of being obtained using a method including a step in which the polyarylene sulfide resin is subjected to a reaction in a molten mixture including a diiodo aromatic compound, elemental sulfur, and a polymerization inhibitor; a production method for said resin composition; and a gasket for a secondary battery.
Description
Technical field
The present invention relates to the pad resin combination, its manufacture method and the secondary cell pad that use in the pad of secondary cell.
Background technology
For enclosed secondary battery, usually the pole plate group comprising positive plate, negative plate and be configured in the barrier film between positive plate and negative plate and the cell device that is used for the electrolyte flooding this pole plate group are received into the inside of the battery container (shell body) of a part of opening, utilize the seal body be used for the opening of battery container seals to come airtight.In addition, in this enclosed secondary battery, such as, at the contact of the contact of positive plate and the positive terminal be electrically connected, negative plate and the negative terminal be electrically connected, in order to prevent the short circuit between pair of terminal, preventing spilling of electrolyte and be provided with pad.For this pad, require the electrolyte resistance to electrolyte, excellent air-tightness.
In order to meet these requirements, such as, report and use the polyamide improving humidity resistance as the technology (for example, see patent documentation 1) of gasket material.But, although improve the polyamide of humidity resistance can improve humidity resistance a little by using, electrolyte resistance and bubble-tight degree still insufficient.
On the other hand, as gasket material, report the pad employing polyarylene sulfide resin or tetrafluoroethylene-perfluoroalkyl vinyl ether copolymer resin and there is excellent air-tightness, electrolyte resistance (for example, see patent documentation 2).
Prior art document
Patent documentation
Patent documentation 1: Japanese Unexamined Patent Publication 2005-78890 publication
Patent documentation 2: Japanese Unexamined Patent Publication 8-321287 publication
Summary of the invention
the problem that invention will solve
In recent years, by using the active material of high theoretical capacity to make the high capacity of lithium ion battery be in progress as electrode substance, and on the other hand, show 3 ~ 4 times of so large change in volume when discharge and recharge, the pressure of interior media becomes very high.In addition, the proportion of the vehicle-mounted purposes of hybrid vehicle (HV), electric automobile (EV) and so on uprises, result requires higher fail safe, requires that the bubble-tight reliability for pad under hot and humid harsh condition is high level gradually.
But existing gasket material cannot tolerate the pressure of interior media, do not reach the level that the enclosed secondary batteries such as lithium rechargeable battery (storage battery) are required required in recent years, insufficient as material.Therefore, gasket material is required to improve mechanical strength.
On the other hand, when there is the injection moulding of the mould of multiple cavity by use and multiple pad be shaped simultaneously, sometimes produce and fully cannot fill the such cob webbing of molding material at a part of cavity.Therefore, can fill molding material also requirement uniformity.
Therefore, the major subjects that the present invention will solve is, provide cavity harmonious excellent and the pad resin combination with high mechanical properties as the material for gasket used in the enclosed secondary batteries such as lithium rechargeable battery (storage battery), its manufacture method and secondary cell pad.
for the scheme of dealing with problems
The present inventor etc. have carried out various research, found that: by using the resin combination of polyarylene sulfide resin and the organo-silicon compound obtained containing making diiodo-aromatic compound, elemental sulfur and polymerization inhibitor melt polymerization, above-mentioned problem can be solved, thus complete the present invention.
Namely, the invention provides a kind of pad resin combination, it is the pad resin combination used in the secondary cell be made up of positive pole, negative pole, seal body, pad, barrier film and electrolyte, described pad resin combination contains polyarylene sulfide resin and organo-silicon compound, polyarylene sulfide resin can obtain by the following method, and described method comprises the operation that diiodo-aromatic compound, elemental sulfur and polymerization inhibitor are reacted in the molten mixture containing diiodo-aromatic compound, elemental sulfur and polymerization inhibitor.The present invention also provides a kind of secondary cell pad formed by above-mentioned pad resin combination.
The present invention also provides a kind of manufacture method of pad resin combination, it is the manufacture method of the pad resin combination used in the secondary cell be made up of positive pole, negative pole, seal body, pad, barrier film and electrolyte, described method has the operation by polyarylene sulfide resin and organo-silicon compound mixing, polyarylene sulfide resin can obtain by the following method, and described method comprises the operation that diiodo-aromatic compound, elemental sulfur and polymerization inhibitor are reacted in the molten mixture containing diiodo-aromatic compound, elemental sulfur and polymerization inhibitor.
the effect of invention
According to the present invention, cavity can be provided harmonious excellent and the pad resin combination with high mechanical properties as the material for gasket used in the enclosed secondary batteries such as lithium rechargeable battery (storage battery), its manufacture method and secondary cell pad.In addition, by using above-mentioned pad resin combination, the secondary cell pad that inhibit by heating the gas generation caused can be made.
Accompanying drawing explanation
Fig. 1 is the schematic diagram that the test film used in compression stress relaxation test is shown.
Embodiment
Below, the preferred embodiment of the present invention is described in detail.But the present invention is not limited to following execution mode.
The pad resin combination of present embodiment contains polyarylene sulfide resin and organo-silicon compound.
The polyarylene sulfide resin used in present embodiment can obtain by the following method, and described method comprises the operation that diiodo-aromatic compound, elemental sulfur and polymerization inhibitor are reacted in the molten mixture containing diiodo-aromatic compound, elemental sulfur and polymerization inhibitor.Utilize such method, the existing Measures compare with being representative with Karen Phillips method (Phillipsmethod), can obtain polyarylene sulfide resin with the form of the polymer than higher molecular weight.
Diiodo-aromatic compound has aromatic ring and 2 atomic iodine with aromatic ring Direct Bonding.As diiodo-aromatic compound, diiodo-benzene, two iodotoluenes, diiodo-dimethylbenzene, diiodonaphthalene, diiodobiphenyl, diiodobenzophenone, diiodo-diphenyl ether and diiodo-diphenyl sulphone (DPS) etc. can be enumerated, but be not limited to these.The position of substitution of 2 atomic iodine is not particularly limited, it is desirable that preferably 2 the position of substitution are positioned at position far away as far as possible in molecule.Preferred the position of substitution is contraposition and 4,4 '-position.
At least a kind of substituting group that the aromatic ring of diiodo-aromatic compound can be selected from halogen atom beyond phenyl, atomic iodine, hydroxyl, nitro, amino, the alkoxyl of carbon number 1 ~ 6, carboxyl, carboxylate, aryl sulfone (arylsulfone) and aryl ketones replaces.But, from the viewpoint such as degree of crystallinity and thermal endurance of polyarylene sulfide resin, the diiodo-aromatic compound be substituted is preferably the scope of 0.0001 ~ 5 quality % relative to the ratio of unsubstituted diiodo-aromatic compound, is more preferably the scope of 0.001 ~ 1 quality %.
Elemental sulfur refers to the material (S be only made up of sulphur atom
8, S
6, S
4, S
2deng), its form is not particularly limited.Specifically, the elemental sulfur that pharmacopeia medicine is commercially available can be used as, also can use can universally obtain containing S
8and S
6deng mixture.The purity of elemental sulfur is also not particularly limited.As long as elemental sulfur is solid under room temperature (23 DEG C), then it can be particle shape shape or Powdered.The particle diameter of elemental sulfur is not particularly limited, and is preferably the scope of 0.001 ~ 10mm, is more preferably the scope of scope, the more preferably 0.01 ~ 3mm of 0.01 ~ 5mm.
As long as polymerization inhibitor suppresses or stops the compound of this polymerization reaction in the polymerization reaction of polyarylene sulfide resin, just can use without particular limitation.Polymerization inhibitor preferably comprises the compound that can import at least one group in the combination selecting the salt of free hydroxyl, amino, carboxyl and carboxyl to form at the end of the main chain of polyarylene sulfide resin.That is, as polymerization inhibitor, preferably there is the compound of at least one group in the group selecting the salt of free hydroxyl, amino, carboxyl and carboxyl to form of more than 1 or 2.In addition, polymerization inhibitor can have above-mentioned functional group, also can generate above-mentioned functional group by the cessation reaction of polymerization etc.
As the polymerization inhibitor with hydroxyl or amino, such as, following formula (1) or the compound shown in (2) can be used as polymerization inhibitor.
Utilize the compound shown in general formula (1), the end group of the univalent perssad shown in following formula (1-1) as main chain can be imported.Y in formula (1-1) is the hydroxyl, amino etc. that are derived from polymerization inhibitor.
Utilize the compound shown in general formula (2), the end group of the univalent perssad shown in following formula (2-1) as main chain can be imported.The hydroxyl being derived from the compound shown in general formula (1) such as can the carbon atom of carbonyl in through type (2) and Thiyl Radical bonding and be imported in polyarylene sulfide resin.
For the group shown in formula (1-1) or (2-1), think the disulfide bond that exists by being derived from raw material (elemental sulfur) in the main chain of polyarylene sulfide resin free radical cracking and the compound shown in the Thiyl Radical that produces and general formula (1) or the compound bonding shown in general formula (2) and be imported in polyarylene sulfide resin under melt temperature.The existence of the construction unit of these ad hoc structures is melt polymerization by employing the compound shown in general formula (1) or (2) and the feature of the polyarylene sulfide resin obtained.
As the compound shown in general formula (1), such as, can enumerate 2-iodophenol, 2-amino aniline etc.As the compound shown in general formula (2), 2-iodine benzophenone can be enumerated.
As the polymerization inhibitor with carboxyl, such as, can use the compound of more than a kind be selected from following general formula (3), (4) or the compound shown in (5).
In general formula (3), R
1and R
2represent hydrogen atom or following general formula (a), the univalent perssad shown in (b) or (c) independently of one another, R
1or R
2at least any one be general formula (a), the univalent perssad shown in (b) or (c).In general formula (4), Z represents atomic iodine or sulfydryl, R
3represent the univalent perssad shown in following general formula (a), (b) or (c).In general formula (5), R
4represent general formula (a), the univalent perssad shown in (b) or (c).
X in general formula (a) ~ (c) is hydrogen atom or alkali metal atom, becomes good aspect from reactivity, preferred hydrogen atom.As alkali metal atom, sodium, lithium, potassium, rubidium and caesium etc. can be enumerated, preferred sodium.In general formula (b), R
10represent the alkyl of carbon number 1 ~ 6.In general formula (c), R
11represent the alkyl of hydrogen atom or carbon number 1 ~ 3, R
12represent the alkyl of carbon number 1 ~ 5.
Utilize general formula (3), (4) or the compound shown in (5), following formula (6) or the univalent perssad shown in (7) end group as main chain can be imported.The existence of the construction unit of the end of these ad hoc structures is the features of the polyarylene sulfide resin obtained by using the melt polymerization of the compound shown in general formula (3), (4) or (5).
(in formula, R
5represent general formula (a), the univalent perssad shown in (b) or (c).)
(in formula, R
6represent general formula (a), the univalent perssad shown in (b) or (c).)
As polymerization inhibitor, the compound etc. without functional groups such as carboxyls can be used.As such compound, such as can use and be selected from diphenyl disulfide, single iodobenzene, benzenethiol, 2,2 '-dibenzothiazyl disulfide, 2-mercaptobenzothiazole, N cyclohexyl 2 benzothiazole sulfenamide, 2-(morpholinothio) benzothiazole and N, at least a kind of compound in N '-dicyclohexyl-1,3-benzothiazole-2-sulfenamide.
The polyarylene sulfide resin of present embodiment generates as follows: carry out melt polymerization in the molten mixture obtained comprising the mixture heating of diiodo-aromatic compound, elemental sulfur, polymerization inhibitor and the catalyst that adds as required, thus generate.For the ratio of the diiodo-aromatic compound in molten mixture, relative to elemental sulfur 1 mole, be preferably the scope of 0.5 ~ 2 mole, be more preferably the scope of 0.8 ~ 1.2 mole.In addition, for the ratio of the polymerization inhibitor in mixture, relative to solid sulfur 1 mole, be preferably the scope of 0.0001 ~ 0.1 mole, be more preferably the scope of 0.0005 ~ 0.05 mole.
Add and be not particularly limited in period of polymerization inhibitor, can by comprising diiodo-aromatic compound, elemental sulfur and the mixture heating of catalyst added as required, the temperature of mixture adds polymerization inhibitor when becoming scope, the more preferably scope of 250 ~ 320 DEG C of preferably 200 DEG C ~ 320 DEG C.
Nitro compound can be added as catalyst to regulate polymerization speed in molten mixture.As this nitro compound, usually various nitrobenzene derivative can be used.As nitrobenzene derivative, such as, can enumerate 1,3-bis-iodo-4-nitrobenzene, 1-iodo-4-nitrobenzene, 2,6-bis-iodo-4-nitrophenols and the iodo-4-nitra-amine of 2,6-bis-.The amount of catalyst is the amount of adding usually used as catalyst, such as, relative to elemental sulfur 100 mass parts, is preferably the scope of 0.01 ~ 20 mass parts.
Suitable adjustment is carried out to the condition of melt polymerization, polymerization reaction is suitably carried out.The temperature of melt polymerization is preferably more than 175 DEG C and the scope of fusing point less than+100 DEG C of polyarylene sulfide resin for generating, is more preferably the scope of 180 ~ 350 DEG C.Melt polymerization is preferably in the scope of scope, more preferably 13 [cPa] ~ 60 [kPa] of 1 [cPa] ~ 100 [kPa] in absolute pressure and carries out.The condition of melt polymerization does not need to fix.Such as, for the polymerization initial stage, temperature can be made to be scope, the more preferably scope of 180 ~ 250 DEG C of preferably 175 ~ 270 DEG C, and, absolute pressure is made to be the scope of 6.7 ~ 100 [kPa], then, heat up continuously or periodically in limit and limit of reducing pressure is polymerized, for the polymerization later stage, temperature is made to be preferably more than 270 DEG C and scope, the more preferably scope of 300 ~ 350 DEG C of the fusing point less than+100 DEG C of polyarylene sulfide resin for generating, further, absolute pressure is made to be that the scope of 1 [cPa] ~ 6 [kPa] is polymerized.In this specification, the fusing point of resin refers to the value using differential scanning calorimetry (DSC) (the DSC device PyrisDiamond that PerkinElmerCo., Ltd. manufacture), measure according to JISK7121.
For melt polymerization, from the view point of preventing oxidation cross-linked reaction and obtaining high polymerization degree, preferably carry out under non-oxidizing atmosphere.In non-oxidizing atmosphere, the oxygen concentration of gas phase is preferably less than the scope of 5 volume %, is more preferably the scope, the further preferred oxygen-free in fact gas of gas phase that are less than 2 volume %.Non-oxidizing atmosphere is preferably the non-active gas atmosphere such as nitrogen, helium and argon.
Melt polymerization such as can use the melting mixing machine possessing heater, decompressor and agitating device to carry out.As melting mixing machine, such as, can enumerate Banbury mixer, kneader, continuous mixer, single screw extrusion machine and double screw extruder.
Molten mixture for melt polymerization does not preferably contain solvent in fact.More specifically, the amount of the solvent contained in molten mixture relative to diiodo-aromatic compound, elemental sulfur, polymerization inhibitor and total 100 mass parts of catalyst of adding as required, the scope being preferably below 10 mass parts, be more preferably below 5 mass parts scope, more preferably 1 mass parts below scope.The amount of solvent can be the scope more than scope of more than more than 0 mass parts, 0.01 mass parts or 0.1 mass parts.
Also molten mixture (product) cooling after melt polymerization, after obtaining the mixture of solid state, under reduced pressure or under the atmospheric pressure of non-oxidizing atmosphere, can added hot mixt thus polymerization reaction is carried out further.Thus, molecular weight can not only be increased further, and the iodine molecule generated distils and is removed, therefore, it is possible to by the atomic iodine control of the concentration in polyarylene sulfide resin at reduced levels.By being cooled to scope, more preferably scope, the further preferred temperature of scope of 150 ~ 230 DEG C of 130 ~ 250 DEG C of preferably 100 ~ 260 DEG C, the mixture of solid state can be obtained.Cooled heating to solid state can be carried out at the temperature same with melt polymerization and pressure condition.
The product comprising the polyarylene sulfide resin obtained by melt polymerization operation also be may be used for directly dropping into the methods such as melting mixing machine by keeping intact and manufactures resin combination, but in this product, add the solvent of this product of dissolving to prepare dissolved matter, when taking out product with the state of this dissolved matter from reaction unit, not only productivity ratio is excellent and then reactivity is also good, therefore preferably.The interpolation of the solvent of this solubilizing reaction product is preferably carried out after melt polymerization, but also can carry out in the reaction later stage of melt polymerization, in addition, also can as mentioned above molten mixture (product) being cooled after obtaining the mixture of solid state, under elevated pressure, decompression under or non-oxidizing atmosphere atmospheric pressure under, add hot mixt and make polymerization reaction carry out rear interpolation further.The operation preparing this dissolved matter can be carried out under non-oxidizing atmosphere.In addition, as the temperature of heating for dissolving, as long as the scope more than the fusing point of solvent dissolving previous reaction product, preferably, preferably 200 ~ 350 DEG C scope, be more preferably the scope of 210 ~ 250 DEG C, add pressure and carry out.
For the compounding ratio using, dissolve the solvent of previous reaction product in order to prepare aforementioned dissolved matter, relative to product 100 mass parts comprising polyarylene sulfide resin, be preferably the scope of 90 ~ 1000 mass parts, be more preferably the scope of 200 ~ 400 mass parts.
As the solvent of solubilizing reaction product, such as, can be used in the polymerisation in solutions such as Karen Phillips method as the solvent that polymerization solvent uses.As the example of preferred solvent, can enumerate: METHYLPYRROLIDONE (hereinafter abbreviated as NMP), CHP, 2-Pyrrolidone, 1, 3-dimethyl-2-imidazolidinone, epsilon-caprolactams, the aliphatic cyclic amide compounds such as N-methyl-E-caprolactam, HPT (HMPA), tetramethylurea (TMU), dimethyl formamide (DMF), and the amide compound such as dimethylacetylamide (DMA), (degree of polymerization is less than 2000 to dialkylethers, there is the alkyl of carbon number 1 ~ 20) etc. etherificate polyethylene glycol compound, and tetramethylene sulfoxide, and the sulfoxide compound such as dimethyl sulfoxide (DMSO) (DMSO).As the example of other spendable solvents, the solvent of more than a kind in the group being selected from and being made up of following material can be enumerated: benzophenone, diphenyl ether, diphenyl sulfide, 4,4 '-'-dibromobiphenyl, 1-phenylnaphthalene, 2,5-diphenyl-1,3,4-oxadiazoles, 2,5-diphenyl-oxazole, triphenylcarbinol, N, N-diphenylformamide, benzil, anthracene, 4-benzoyl biphenyl, dibenzoyl methane, 2-biphenyl carboxylic acids, dibenzothiophenes, pentachlorophenol, 1-benzyl-2-Pyrrolidone, 9-Fluorenone, 2-benzoyl naphthalene, 1-bromonaphthalene, 1,3-bis-phenoxy group benzene, fluorenes, 1-phenyl-2-Pyrrolidone, 1-methoxynaphthalene, 1-ethyoxyl naphthalene, 1,3-diphenyl acetone, Isosorbide-5-Nitrae-dibenzoyl butane, luxuriant and rich with fragrance, 4-benzoyl biphenyl, 1,1-diphenyl acetone, o, o '-xenol, 2,6-diphenylphenol, benzophenanthrene, 2-phenylphenol, thianthrene, 3-phenoxy benzenemethanol, 4-phenylphenol, 9,10-bis-chrloroanthracene, triphenyl methane, 4,4 '-dimethoxy-benzophenone, 9,10-diphenylanthrancene, fluoranthene, diphenyl phthalate, diphenyl carbonate, 2,6-dimethoxy-naphthalene, 2,7-dimethoxy-naphthalene, 4-dibromodiphenyl ether, pyrene, 9,9 '-two fluorenes, 4,4 '-isopropylidene-biphenol, epsilon-caprolactams, CHP, diphenyl iso-phthalate, phthalic acid diphenyl and 1-chloronaphthalene.
From reaction unit take out this dissolved matter after carrying out reprocessing, with other components fuse aforementioned are mixing prepare resin combination time, reactivity becomes better, therefore preferably.As the method for the reprocessing of dissolved matter, be not particularly limited, such as, can enumerate following methods.
(1) after this dissolved matter is kept intact or adding acid or alkali, distillation is except desolventizing under reduced pressure or under atmospheric pressure, then, by the solid matter after solvent distillation removing with being selected from the solvent (or there is relative to low polymer the organic solvent of equal solubility), the solvent wash more than 1 time or 2 times in acetone, methylethylketone and alcohols etc. that use in water, this dissolved matter, and then carry out neutralizing, wash, filter and the method for drying.
(2) in this dissolved matter, water, acetone, methylethylketone, alcohol, ether, halogenated hydrocarbons, aromatic hydrocarbon and aliphatic hydrocarbon equal solvent (dissolve in the solvent of this dissolved matter and be at least the solvent of poor solvent for polyarylene sulfide resin) is added as sedimentation agent, make the solid product sedimentation comprising polyarylene sulfide resin and inorganic salts etc., solid product filtered, washing and the method for drying.
(3) add after the solvent (or having the organic solvent of equal solubility relative to low polymer) used in this dissolved matter stirs in this dissolved matter, filter and remove low-molecular weight polymer, then with the solvent wash more than 1 time or 2 times be selected from water, acetone, methylethylketone and alcohol etc., then carry out neutralizing, wash, filter and the method for drying.
It should be noted that, in post-processing approach such above-mentioned (1) ~ (3) Suo Lishi, the drying of polyarylene sulfide resin can be carried out in a vacuum, also can carry out in atmosphere or in the non-active gas atmosphere of nitrogen and so on.Also can be in the oxidizing atmosphere of the scope of 5 ~ 30 volume % in oxygen concentration or heat-treat under reduced pressure, make polyarylene sulfide resin oxidation cross-linked.
Below exemplify the reaction that polyarylene sulfide resin is generated by melt polymerization.
Reaction equation (1)
Reaction equation (2)
Reaction equation (3)
Reaction equation (4)
Reaction equation (5)
2l’→l
2
Reaction equation (1) ~ (5) be use the diphenyl disulfide such as with the substituent R comprising the group shown in general formula (a), (b) or (c) as during polymerization inhibitor, the example of the reaction that generates polyphenylene sulfide.Reaction equation (1) is that in polymerization inhibitor ,-S-S-key issues the reaction of being conigenous by basic capsule solution in melt temperature.Reaction equation (2) is that the Thiyl Radical produced in reaction equation (1) attacks the adjacent carbon atom of the end atomic iodine of the main chain in growth and atomic iodine departs from, thus imports the reaction of substituent R at the end of main chain while polymerization is stopped.Reaction equation (3) is that the disulfide bond existed from raw material (elemental sulfur) in the main chain of polyarylene sulfide resin issues the reaction of being conigenous by basic capsule solution in melt temperature.Reaction equation (4) is Thiyl Radical by producing in reaction equation (3) and the bonding again of the middle Thiyl Radical produced of reaction equation (1) and make to be polymerized the reaction stopping, substituent R being imported simultaneously the end of main chain.The atomic iodine departed from is in free state (iodine free radical) or iodine free radical passes through bonding each other again and generates iodine molecule as reaction equation (5).
The product comprising the polyarylene sulfide resin obtained by melt polymerization contains the atomic iodine being derived from raw material.Therefore, polyarylene sulfide resin is used to the preparation etc. of spinning resin combination usually with the state of the mixture containing atomic iodine.The concentration of the atomic iodine in this mixture is such as the scope of scope, the preferably 10 ~ 5000ppm of 0.01 ~ 10000ppm relative to polyarylene sulfide resin.Utilizing the sublimability of iodine molecule, can, by atomic iodine control of the concentration at reduced levels, in this case, also can be also the scope of the scope of the scope of below 900ppm, preferably below 100ppm, further preferred below 10ppm.And then, although also below atomic iodine to detectability can be removed, impracticable when considering productivity ratio.Detectability is such as about 0.01ppm.For the present embodiment obtained by melt polymerization polyarylene sulfide resin or comprise its product, comprising this point of atomic iodine, such as can with by the solution polymerization process of the dichloro aromatic compounds such as Karen Phillips method in organic polar solvent and the poly arylidene thio-ester obtained distinguish clearly.
Also be appreciated that the polyarylene sulfide resin obtained by melt polymerization is comprised by above-mentioned reaction equation: the main chain formed primarily of fragrant thio-ether units; And the substituent R of regulation with the end bonding of this main chain, described fragrant thio-ether units contains the aromatic ring that is derived from diiodo-aromatic compound and the sulphur atom with its Direct Bonding.Regulation substituent R Direct Bonding or be bonded to by the part-structure being derived from polymerization inhibitor on the aromatic ring of end of main chain.
As the polyphenylene sulfide of the polyarylene sulfide resin of an execution mode, such as, there is the main chain comprising the repetitive (fragrant thio-ether units) shown in following general formula (10).
Repetitive shown in formula (10) is more preferably with the repetitive shown in the following formula of para-linkage (10a) and with the repetitive shown in the following formula of ortho position bonding (10b).
Wherein, shown in formula (10a) with the repetitive of para-linkage resin thermal endurance and crystalline in preferred.
Polyphenylene sulfide described in an execution mode can comprise shown in following general formula (11), there is substituent repetitive as the side chain with aromatic ring bonding:
(in formula, R
20and R
21represent hydrogen atom, the alkyl of carbon number 1 ~ 4, nitro, amino, phenyl, methoxy or ethoxy independently of one another.)。
But reduce from the view point of degree of crystallinity and thermal endurance, polyphenylene sulfide is not preferably in fact containing the repetitive of general formula (11).More specifically, about the ratio of the repetitive shown in formula (11), relative to the summation of the repetitive shown in the repetitive shown in formula (10) and formula (11), be preferably below 2 quality %, be more preferably below 0.2 quality %.
The polyarylene sulfide resin of present embodiment is formed primarily of above-mentioned fragrant thio-ether units, in main chain, usually also comprise construction unit that be derived from the elemental sulfur of raw material, the disulfide bond shown in following formula (20).
From the aspect of thermal endurance, mechanical strength, about the ratio of the construction unit shown in formula (20), relative to the summation of the construction unit shown in fragrant thio-ether units and formula (20), be preferably the scope of below 2.9 quality %, be more preferably the scope of below 1.2 quality %.
The Mw/Mtop of the polyarylene sulfide resin of present embodiment is preferably the scope of 0.80 ~ 1.70, is more preferably the scope of 0.90 ~ 1.30.By making Mw/Mtop be such scope, the processability of polyarylene sulfide resin can be improved, good cavity can be given harmonious.In this specification, Mw represents the weight average molecular weight by gel permeation chromatography, and Mtop represents that the detected intensity of the chromatogram obtained by this mensuration becomes the mean molecule quantity (peak molecular weight) of maximum point.Mw/Mtop represents the distribution of the molecular weight of determination object, usually, this value close to 1 time represent the narrowly distributing of molecular weight, along with this value becomes large, represent that the distribution of molecular weight broadens.It should be noted that, the condition determination of gel permeation chromatography adopts the condition determination identical with the embodiment of this specification.But, substantially can not affect the scope interior change condition determination of the value of Mw, Mw/Mtop.
The weight average molecular weight of the polyarylene sulfide resin of present embodiment only otherwise damage effect of the present invention, is just not particularly limited, for its lower limit, from the aspect of mechanical strength, be preferably more than 28000 so that be more preferably more than 30000 scope.On the other hand, for the upper limit, from giving better cavity balanced aspect, be preferably the scope of less than 100000, and then be more preferably the scope of less than 60000, and then most preferably be the scope of less than 55000.And then, can give good cavity balanced viewpoint from mechanical strength, can with 28000 ~ 60000 scope polyarylene sulfide resin, more preferably 30000 ~ 55000 scope polyarylene sulfide resin together with use weight average molecular weight to be in more than 60000 and be the polyarylene sulfide resin of the scope of less than 100000.
The non-newtonian index of polyarylene sulfide resin is preferably the scope of 0.95 ~ 1.75, is more preferably the scope of 1.00 ~ 1.70.By making non-newtonian index be such scope, the processability of polyarylene sulfide resin can be improved, good cavity can be given harmonious.In this specification, non-newtonian index refers to the index of the following relational expression of shear rate under the condition of satisfied temperature 300 DEG C and shear stress.Non-newtonian index can become the molecular weight of determination object or straight chain, side chain, index that crosslinked such molecular structure is relevant.Usually, this value close to 1 time, represent that the molecular results of resin is straight-chain, along with this value becomes large, represent and comprise more side chain, cross-linked structure.
D=α×S
n
(in above-mentioned formula, D represents shear rate, and S represents shear stress, and α represents constant, and n represents non-newtonian index.)
The polyarylene sulfide resin of the Mw/Mtop and non-newtonian index with above-mentioned particular range such as can obtain as follows: react in the molten mixture containing diiodo-aromatic compound, elemental sulfur and polymerization inhibitor in the method for (polymerisation in solution) making diiodo-aromatic compound, elemental sulfur and polymerization inhibitor, make the macromolecule quantification to a certain degree of described polyarylene sulfide resin, thus obtain.
The fusing point of polyarylene sulfide resin is preferably the scope of 250 ~ 300 DEG C, is more preferably the scope of 265 ~ 300 DEG C.The melt viscosity (V6) of 300 DEG C of polyarylene sulfide resin is preferably the scope of 1 ~ 2000 [Pas], is more preferably the scope of 5 ~ 1700 [Pas].Herein, melt viscosity (V6) refer to use flow tester, serviceability temperature 300 DEG C, load 1.96MPa, Kong Changyu bore dia ratio (hole length/bore dia) be 10/1 hole keep the melt viscosity after 6 minutes.
As the organo-silicon compound used in present embodiment, preferred main chain has the polysiloxane shown in following general formula (I) of siloxane bond.
R
30-〔Si(R
31)
2-O〕n
1-R
32(I)
(in formula, R
30, R
31and R
32represent hydrogen atom or organic group independently of one another, n
1it is the integer of more than 2.)
Wherein, the R particularly preferably in above-mentioned general formula (1)
30, R
31and R
32be all the dimethyl silicone polymer of methyl, also a preferred part by the methyl of this dimethyl silicone polymer replaces with hydrogen atom or other substituent polysiloxane.
As other substituting groups, the alkyl of carbon number more than 2, aryl, haloalkyl, silyl alkyl, polyoxyalkylenes and reactive functional groups can be enumerated, when replacing multiple methyl, therefrom can be selected from and communicate with each other or different substituting groups.
As the alkyl of carbon number more than 2, such as, can enumerate ethyl, propyl group, butyl, octyl group, dodecyl etc.As aryl, such as, can enumerate phenyl, tolyl, naphthyl etc.
As haloalkyl, such as, fluoropropyl, chloropropyl etc. can be enumerated.
For silyl alkyl, the group shown in following general formula (II) can be enumerated as its representational concrete example.
-(CH
2)n
2-Si(OCH
3)
3(II)
(in formula, n
2it is the integer of more than 1.)
For polyoxyalkylenes, the group shown in following general formula (III) can be enumerated as its concrete example.
-〔CH
2〕k-O-〔C
2H
4O〕l-〔C
3H
6O〕m-R
33(III)
(in formula, k, l and m are 0 or positive integer independently of one another, are the integer of 0 when l and m gets difference.In addition, R
33for being selected from more than a kind substituting group in the group that is made up of hydrogen atom, alkyl, aryl, haloalkyl, silyl alkyl and reactive functional groups described later.)
Organo-silicon compound preferably have reactive functional groups.As the concrete example of reactive functional groups, epoxy radicals, amino, sulfydryl, vinyl, carboxyl, hydroxyl, NCO, amide groups, acyl group, itrile group, anhydride group etc. can be enumerated.These reactive functional groups can be bonded directly on main chain, or also can be bonded to the end of the organic group such as alkylidene, polyoxyalkylenes of bonding on main chain.Wherein, particularly preferably carboxyl, hydroxyl, epoxy radicals and amino, further preferred epoxy radicals and amino.
Organo-silicon compound by disperseing equably thus playing the effect improved the durability of electrolyte in resin combination, from this viewpoint, the viscosity (25 DEG C) of organo-silicon compound is preferably 10 ~ 100000mPas, is particularly preferably in the material of the oily of the scope of 10 ~ 80000mPas.It should be noted that, in order to make organo-silicon compound dispersed in the resin combination of present embodiment, preferably making organo-silicon compound be carried on the inorganic particles such as silicon dioxide and the material that obtains.
Time in organo-silicon compound containing reactive functional groups, the good dispersion of organo-silicon compound in resin combination, therefore, it is possible to realize the raising of resistance to impact.And then to suppress organo-silicon compound to ooze out into products formed surface, the so-called aspect oozing out (bleedout) effect also preferred from having.
For the containing ratio of the reactive functional groups in organo-silicon compound, from by giving resistance to impact, obdurability and obtain the aspect of desirable effect, be preferably more than 400g/ equivalent (hereinafter abbreviated as " g/eq "), from the aspect of mixing easiness, be preferably below 50000g/eq.
In addition, about the compounding amount of organo-silicon compound, relative to summation 100 mass parts of polyarylene sulfide resin and organo-silicon compound, be preferably 0.1 ~ 10 mass parts, be more preferably 0.3 ~ 5 mass parts, more preferably 0.5 ~ 3 mass parts.
Can compounding silane compound in the pad resin combination of present embodiment.As silane compound, such as, can enumerate aminoalkoxysilane, epoxy radicals alkoxy silane, vinyl alkoxy silane etc.These silane compounds may be used singly or in combination of two or more.
As aminoalkoxysilane, as long as there is more than 1 the amino and silane compound with more than 2 alkoxyls in 1 molecule just can use, such as can enumerate: γ aminopropyltriethoxy silane, gamma-amino propyl trimethoxy silicane, gamma-amino hydroxypropyl methyl diethoxy silane, gamma-amino hydroxypropyl methyl dimethoxysilane, N-β (amino-ethyl)-γ aminopropyltriethoxy silane, N-β (amino-ethyl)-gamma-amino propyl trimethoxy silicane, N-β (amino-ethyl)-gamma-amino hydroxypropyl methyl diethoxy silane, N-β (amino-ethyl)-gamma-amino hydroxypropyl methyl dimethoxysilane, N-phenyl-γ aminopropyltriethoxy silane, N-phenyl-gamma-amino propyl trimethoxy silicane etc.
As epoxy radicals alkoxy silane, as long as there is in 1 molecule more than 1 epoxy radicals and the silane compound with more than 2 alkoxyls just can use, such as can enumerate: γ-glycidoxypropyltrime,hoxysilane, β-(3,4-epoxycyclohexyl) ethyl trimethoxy silane, γ-glycidoxypropyl group triethoxysilane, γ-glycidoxypropyl diethoxy silane, γ-glycidoxypropyl dimethoxysilane etc.
As vinyl alkoxy silane, as long as there is in 1 molecule more than 1 vinyl and the silane compound with more than 2 alkoxyls just can use, such as, can enumerate vinyltriethoxysilane, vinyltrimethoxy silane, vinyl three ('beta '-methoxy ethyoxyl) silane etc.
In present embodiment, except above-mentioned each composition, fibrous reinforcements or inanimate matter filler can be added in the scope not damaging the effect that the present invention plays.
As fibrous reinforcements, such as, can enumerate: the organic fibrous material such as inorganic fibre shape material and aramid fiber of the fibrous material of the metal such as carbon fiber, silicon dioxide fibre, silica alumina fiber, Zirconium oxide fibre, boron nitride fiber, silicon nitride fiber, boron fibre, aluminum borate fiber, potassium titanate fibre, stainless steel, aluminium, titanium, copper, brass of glass fibre, PAN system or asphalt series.
As inanimate matter filler, such as, can enumerate: the metal oxides such as the sulfate such as the carbonate such as the silicate such as mica, talcum, wollastonite, sericite, kaolin, clay, bentonite, asbestos, alumina silicate, zeolite, pyrophyllite, calcium carbonate, magnesium carbonate, dolomite, calcium sulfate, barium sulfate, aluminium oxide, magnesium oxide, silicon dioxide, zirconia, titanium dioxide, iron oxide, bead, ceramic bead, boron nitride, carborundum, calcium phosphate etc.These fibrous reinforcements and inanimate matter filler may be used singly or in combination of two or more.
In addition, in the pad resin combination of present embodiment, can in the scope not damaging the effect that the present invention plays appropriate compounding antioxidant, stabilizer, processing heat stabilizer, plasticizer, release agent, colouring agent, lubricant, weatherability stabilizer, blowing agent, rust inhibitor, wax.
And then, in the pad resin combination of present embodiment, required characteristic suitably other resinous principles compounding can be coordinated.As operable resinous principle herein, can enumerate: ethene, butylene, amylene, butadiene, isoprene, chlorobutadiene, styrene, AMS, vinyl acetate, vinyl chloride, acrylate, methacrylate, the homopolymers of the monomers such as (methyl) acrylonitrile or copolymer, polyurethane, polybutylene terephthalate (PBT), the polyester such as PETG, polyacetals, Merlon, polysulfones, polyarylsulfone (PAS), polyether sulfone, polyphenylene oxide, polyether-ketone, polyether-ether-ketone, polyimides, polyamidoimide, Polyetherimide, organic siliconresin, epoxy resin, phenoxy resin, liquid crystal polymer, the homopolymers such as polyarylether, random copolymer or block copolymer, graft copolymer etc.
As the method for the pad resin combination of manufacture present embodiment, specifically, following method can be enumerated: use rotary drum, Henschel mixer etc. by organo-silicon compound, polyarylene sulfide resin and other compounding as required compounding ingredients Homogeneous phase mixing, then this mixture is put in double screw extruder, under the discharge rate (kg/hr) of resinous principle and the ratio (discharge rate/screw speed) of screw speed (rpm) are the condition of the scope of 0.02 ~ 0.2 (kg/hrrpm), carry out melting mixing.
For above-mentioned manufacture method, further description, can enumerate following method: put in double screw extruder by aforementioned each composition, under the temperature conditions of design temperature 330 DEG C, resin temperature about 350 DEG C, carry out melting mixing.Now, the discharge rate of resinous principle is the scope of 5 ~ 50kg/hr under rotating speed 250rpm.Wherein, particularly from the aspect of dispersiveness, be preferably 20 ~ 35kg/hr.Thus, the discharge rate (kg/hr) of resinous principle and the ratio (discharge rate/screw speed) of screw speed (rpm) are particularly preferably 0.08 ~ 0.14 (kg/hrrpm).
The pad resin combination so carrying out melting mixing is cut into graininess usually.In addition, carry out melt-shaping by the pellet supply that will obtain to forming machine, thus obtain the molding of final goal shape.
Herein, for the method for carrying out melt-shaping, such as, can enumerate injection moulding, extrusion molding, compression molding etc., wherein, as the method that secondary cell is shaped with pad, particularly preferably injection moulding.
The pad resin combination of present embodiment is such as particularly useful to pad of the secondary cell, especially the high-capacity lithium-ion secondary cell that use in the electric equipment purposes such as laptop, mobile phone, video camera or the vehicle-mounted purposes such as hybrid vehicle (HV), electric automobile (EV) etc.
Embodiment
Below, enumerate embodiment and illustrate the present invention further.But the present invention is not limited to these embodiments.
1. polyphenylene sulfide (PPS resin)
The synthesis of 1-1.PPS-1 ~ 5
(synthesis example 1)
By paradiiodobenzene (Tokyo changes into Co., Ltd., paradiiodobenzene purity more than 98.0%) 300.0g, solid sulfur (Kanto Kagaku K. K.'s manufacture, sulphur (powder)) 27.00g, 4, (Wako Pure Chemical Industries, Ltd.'s manufacture, 4 of 4 '-two thiobis benzoic acid, 4 '-two thiobis benzoic acid, TechnicalGrade) 2.0g is heated to 180 DEG C in a nitrogen atmosphere, and they are dissolved and mixes.Then, be warming up to 220 DEG C, be decompressed to absolute pressure 26.6kPa.Periodically temperature and pressure is changed, while heat the molten mixture obtained and carry out melt polymerization 8 hours in the mode that in system, absolute pressure becomes 133Pa at 320 DEG C.After reaction terminates, add NMP200g, at 220 DEG C, add thermal agitation, gained dissolved matter is filtered.Add NMP320g in dissolved matter after filtration, carry out Washing of Filter Cake filtration.Obtain containing NMP filter cake in add ion exchange water 1L, in autoclave, in 200 DEG C stir 10 minutes.Then, filter filter cake, add the ion exchange water 1L of 70 DEG C in filter cake after filtration, carry out Washing of Filter Cake.In the moisture filter cake obtained, add ion exchange water 1L, stir 10 minutes.Then, filter filter cake, add the ion exchange water 1L of 70 DEG C in filter cake after filtration, carry out Washing of Filter Cake.After repeating this operation again, by filter cake at 120 DEG C dry 4 hours, obtain PPS resin 91g.
(synthesis example 2)
Use " 2-Iodoaniline (Tokyo changes into Co., Ltd. and manufactures) " replacement " 4,4 '-two thiobis benzoic acid ", in addition, operate in the same manner as synthesis example 1, obtain PPS resin 91g.
(synthesis example 3)
Use " diphenyl disulfide (Sumitomo Seika Co., Ltd, DPDS) " replacement " 4,4 '-two thiobis benzoic acid ", in addition, operate in the same manner as synthesis example 1, obtain PPS resin 91g.
(synthesis example 4)
Paradiiodobenzene (Tokyo changes into Co., Ltd.'s manufacture, paradiiodobenzene purity more than 98.0%) 300.0g, solid sulfur (Kanto Kagaku K. K.'s manufacture, sulphur (powder)) 29.15g and 4-iodine biphenyl (Tokyo changes into Co., Ltd. and manufactures) 1.48g are heated to 180 DEG C in a nitrogen atmosphere, they are dissolved and mixes.Then, be warming up to 220 DEG C, be decompressed to absolute pressure 46.7kPa, periodically change temperature and pressure, while carry out 8 hours melt polymerizations to the molten mixture heating edge obtained in the mode that in system, absolute pressure becomes 133Pa at 320 DEG C.After reaction terminates, add NMP200g, at 220 DEG C, add thermal agitation, gained dissolved matter is filtered.Add NMP320g in dissolved matter after filtration, carry out Washing of Filter Cake filtration.Obtain containing the filter cake of NMP in add ion exchange water 1L, stir 10 minutes in autoclave, at 200 DEG C.Then, filter filter cake, add the ion exchange water 1L of 70 DEG C in filter cake after filtration, carry out Washing of Filter Cake.In the moisture filter cake obtained, add ion exchange water 1L, stir 10 minutes.Then, filter filter cake, add the ion exchange water 1L of 70 DEG C in filter cake after filtration, carry out Washing of Filter Cake.After repeating this operation again, by filter cake at 120 DEG C dry 4 hours, obtain PPS resin 91g.
(comparing synthesis example)
Drop into NMP600g and five hydrated sodium sulfide 336.3g (2.0mol), be warming up to 200 DEG C in a nitrogen atmosphere, thus dephlegmate-NMP mixture.Then, in this system, solution paracide 292.53g and 2,5-dichloroaniline 1.62g being dissolved in gained in NMP230g is added, in a nitrogen atmosphere, in 220 DEG C of reactions 5 hours, and then in 240 DEG C of reactions 2 hours.After being cooled by reaction vessel, take out content, a sampling part, carries out quantitatively unreacted 2,5-dichloroaniline with gas chromatograph.In addition, with the residual slurry of hot wash several times, leaching polymer cake.By this filter cake drying under reduced pressure at 80 DEG C, obtain pulverous PPS resin.Measure infrared absorption spectroscopy, result is at 3380cm
-1near observe and be regarded as being derived from amino absorption spectrum.
1-2. melt viscosity
Shimadzu Seisakusho Ltd. is used to manufacture flow tester, CFT-500C, at 300 DEG C, load: 1.96 × 10
6keep PPS resin under Pa, L/D=10/1 6 minutes, then measure melt viscosity.
1-3. non-newtonian index
Utilize capillary rheometer, under the condition of temperature 300 DEG C, use the mould of diameter 1mm, long 40mm, PPS resin is measured relative to 100 ~ 1000 (sec
-1) the shear stress of shear rate, the value calculated by the slope of the logarithmic plot of these data.
1-4.Mw and Mw/Mtop (molecular weight distribution)
Use gel permeation chromatography, measured weight average molecular weight and the peak molecular weight of PPS resin by following condition determination.Mw/Mtop is calculated by Mw and Mtop obtained.6 kinds of monodisperse polystyrenes are used for correct.
Device: superhigh temperature polymer molecular weight distribution measurement device (" SSC-7000 " that SenshuScientificCo., Ltd manufacture)
Post: UT-805L (Showa Denko K. K's manufacture)
Column temperature: 210 DEG C
Solvent: 1-chloronaphthalene
Assay method: UV detector (360nm)
The characteristic of PPS-1 ~ 5 of synthesis is gathered and is shown in table 1.
[table 1]
2. polyphenyl thioether resin composition (PPS compound)
2-1. raw material
In order to prepare PPS resin combination, prepare following organo-silicon compound.
Si-1: silicone powder (powder that DowCorningTorayCo., Ltd. manufacture, " TREFILF-202 ", supported on silica have 60 quality % silicone oil (viscosity (25 DEG C) 62Pas))
Si-2: containing amino organosilicon (Shin-Etsu Chemial Co., Ltd's manufacture, " KF-868 ")
The making of 2-2. compound
According to the compounding composition described in table 2, use rotary drum by each raw material Homogeneous phase mixing, then, use twin-screw mixer extruder (Toshiba Machinery Co., Ltd.'s manufacture, " TEM-35B ") melting mixing at 300 DEG C, obtain granular compound.
3. evaluate
3-1. hot strength and tensile elongation
For being the evaluation formed products that ASTM4 dumbbell shape obtains by the compound injection moulding obtained, according to ASTMD638, " AutographAG-5000C " of Shimadzu Scisakusho Ltd's manufacture is used to measure tension fracture elongation rate.
3-2. compression stress relaxation is tested
Use injection machine to be shaped by resin composition pellet, be configured as the flat board of long 8mm × wide 8mm × thick 3mm by injection machine, make compression stress relaxation test film as shown in Figure 1.Use this test film, " AutographAG-50KNX " that utilize the Shimadzu Scisakusho Ltd possessing thermostat to manufacture, (temperature conditions: 23 DEG C and 60 DEG C) mensuration compression stress relaxation under 10% distortion, obtain the compression stress after 100 hours.
The bubble-tight evaluation of 3-3.
Use injection machine shaping resin composition grain, make the box-shaped products formed that shape is long 8mm × wide 8mm × high 10mm and thick 0.8mm.Then, electrolyte (the LiPF6/ ethylene carbonate (EC) of 1mol/L: dimethyl carbonate (DMC) (capacity 1:1 mixed solution) solution, KishidaChemicalCo. is added in this box-shaped products formed, Ltd. manufacture), the air seal test sample that in making compression stress relaxation test, the flat board of the long 8mm × wide 8mm × thick 3mm of use is sealed up with certain stress (under 10% distortion).By its xeothermic lower placement 100 hours at 60 DEG C, confirm the leakage situation of liquid.It should be noted that, evaluation result represents as follows.
The leakage of liquid is not produced after zero: 100 hour.
×: the leakage producing liquid after 100 hours.
3-4. cavity is harmonious
Use the gasket mould with 40 cavitys, as long as the cavity (C1) of the position near a cast gate is filled completely, with minimum molding condition by PPS compound injection moulding.Molding condition be 75 tons of forming machines, barrel temperature 320 DEG C, mold temperature 140 DEG C, without pressurize.
Cavity (C1) after shaping is compared with the compactedness apart from cast gate cavity farthest (C10) being in identical runner.Compactedness (quality %) is obtained relative to the mass ratio of the formed products of cavity (C1) by the formed products of cavity (C10).Can say that the compactedness of cavity (C10) is higher, cavity is harmonious more excellent.Based on compactedness, the cavity of each composition is harmonious to utilize following benchmark to judge.
AA:100 ~ 90 quality %
A:89 ~ 80 quality %
B:79 ~ 70 quality %
C:69 ~ 60 quality %
Below D:59% quality
3-5. produces gas flow
Use gas chromatography-mass spectrum device, for PPS resin monomer and PPS compound, the sample of ormal weight is heated 15 minutes at 325 DEG C, generation gas flow is now carried out quantitatively with the form of quality %.
[table 2]
Result as shown in Table 2 shows, the resin combination cavity made in embodiment is harmonious excellent, can form the formed products that mechanical strength is high, air-tightness is also excellent, when using as pad, can maintain the air-tightness required for secondary cell.
Claims (7)
1. a pad resin combination, it is the pad resin combination used in the secondary cell be made up of positive pole, negative pole, seal body, pad, barrier film and electrolyte,
Described pad resin combination contains polyarylene sulfide resin and organo-silicon compound,
Described polyarylene sulfide resin obtains by following method, and described method comprises the operation making to react in the molten mixture containing described diiodo-aromatic compound, described elemental sulfur and described polymerization inhibitor containing diiodo-aromatic compound, elemental sulfur and polymerization inhibitor.
2. pad resin combination according to claim 1, wherein, described polyarylene sulfide resin has at least one group in the group that salt that be derived from described polymerization inhibitor, that select free hydroxyl, amino, carboxyl and carboxyl forms.
3. pad resin combination according to claim 1 and 2, wherein, described polyarylene sulfide resin has the non-newtonian index of 0.95 ~ 1.75 at 300 DEG C and the Mw/Mtop of 0.80 ~ 1.70,
Described Mw and Mtop is weight average molecular weight by gel permeation chromatography and peak molecular weight respectively.
4. a secondary cell pad, its pad resin combination according to any one of claims 1 to 3 is formed.
5. a manufacture method for pad resin combination, it is the manufacture method of the pad resin combination used in the secondary cell be made up of positive pole, negative pole, seal body, pad, barrier film and electrolyte,
Described method has the operation by polyarylene sulfide resin and organo-silicon compound mixing,
Described polyarylene sulfide resin obtains by following method, and described method comprises the operation that diiodo-aromatic compound, elemental sulfur and polymerization inhibitor are reacted in the molten mixture containing described diiodo-aromatic compound, described elemental sulfur and described polymerization inhibitor.
6. the manufacture method of pad resin combination according to claim 5, wherein, described polyarylene sulfide resin has at least one group in the group that salt that be derived from described polymerization inhibitor, that select free hydroxyl, amino, carboxyl and carboxyl forms.
7. the manufacture method of the pad resin combination according to claim 5 or 6, wherein, described polyarylene sulfide resin has the non-newtonian index of 0.95 ~ 1.75 at 300 DEG C and the Mw/Mtop of 0.80 ~ 1.70,
Described Mw and Mtop is weight average molecular weight by gel permeation chromatography and peak molecular weight respectively.
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US11631915B2 (en) | 2018-02-23 | 2023-04-18 | Lg Energy Solution, Ltd. | Gasket for secondary battery, and secondary battery including the same |
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KR102595639B1 (en) | 2023-10-31 |
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